RU2522458C2 - Тетразольные соединения для снижения концентрации мочевой кислоты - Google Patents
Тетразольные соединения для снижения концентрации мочевой кислоты Download PDFInfo
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- RU2522458C2 RU2522458C2 RU2010148762/04A RU2010148762A RU2522458C2 RU 2522458 C2 RU2522458 C2 RU 2522458C2 RU 2010148762/04 A RU2010148762/04 A RU 2010148762/04A RU 2010148762 A RU2010148762 A RU 2010148762A RU 2522458 C2 RU2522458 C2 RU 2522458C2
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- Prior art keywords
- compound
- dimethylbenzyloxy
- tetrazole
- formula
- group
- Prior art date
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US4916708P | 2008-04-30 | 2008-04-30 | |
| US61/049,167 | 2008-04-30 | ||
| US9374308P | 2008-09-03 | 2008-09-03 | |
| US61/093,743 | 2008-09-03 | ||
| PCT/US2009/042298 WO2009134995A2 (en) | 2008-04-30 | 2009-04-30 | Tetrazole compounds for reducing uric acid |
Publications (2)
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| RU2010148762A RU2010148762A (ru) | 2012-06-10 |
| RU2522458C2 true RU2522458C2 (ru) | 2014-07-10 |
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| CN (1) | CN102014898B (enExample) |
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| BR (1) | BRPI0910541B8 (enExample) |
| CA (1) | CA2722624C (enExample) |
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| WO (1) | WO2009134995A2 (enExample) |
| ZA (1) | ZA201006929B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2683570C1 (ru) * | 2018-05-23 | 2019-03-29 | Евгений Иванович Верещагин | Композиция из растительных компонентов, обладающая способностью снижать уровень мочевой кислоты сыворотки крови |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8829058B2 (en) | 2008-03-13 | 2014-09-09 | Wellstat Therapeutics Corporation | Compounds and method for reducing uric acid |
| MX2010011603A (es) | 2008-04-30 | 2011-01-25 | Wellstat Therapeutics Corp | Compuestos de tetrazol para reducir el acido urico. |
| WO2011046800A1 (en) * | 2009-10-13 | 2011-04-21 | Wellstat Therapeutics Corporation | 3-substituted compounds for reducing uric acid |
| US20130331452A1 (en) | 2010-09-08 | 2013-12-12 | Wellstat Therapeutics Corporation | Benzoic acid compounds for reducing uric acid |
| ES2704233T3 (es) * | 2011-11-03 | 2019-03-15 | Ardea Biosciences Inc | Compuesto de piridina 3,4-di-sustituido, procedimientos de uso y composiciones que comprenden el mismo |
| MX357510B (es) * | 2011-11-04 | 2018-07-12 | Cymabay Therapeutics Inc | Metodos para tratar ataques de gota. |
| WO2013111870A1 (ja) * | 2012-01-27 | 2013-08-01 | 帝人ファーマ株式会社 | 糖尿病の治療薬 |
| TW201443025A (zh) * | 2013-04-19 | 2014-11-16 | Pfizer Ltd | 化學化合物 |
| CN104292176B (zh) * | 2014-10-07 | 2016-06-29 | 张远强 | 一种含卤代苯的四氮唑乙酸类化合物、其制备方法和用途 |
| CN104262277B (zh) * | 2014-10-07 | 2016-06-22 | 张远强 | 含硝基和卤苯取代的四氮唑乙酸类化合物、其制备方法及用途 |
| CN104292177B (zh) * | 2014-10-07 | 2016-08-17 | 张远强 | 含腈基和卤苯取代的四氮唑乙酸类化合物、其制备方法及用途 |
| JP6192142B2 (ja) * | 2016-09-13 | 2017-09-06 | サイマベイ・セラピューティクス・インコーポレイテッドＣｙｍａＢａｙ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． | 痛風発赤の治療方法 |
| CN111943957B (zh) * | 2019-05-17 | 2023-01-06 | 中国医学科学院药物研究所 | 喹啉甲酰胺类化合物及其制备方法和用途 |
| CN114805233A (zh) * | 2022-03-30 | 2022-07-29 | 华南理工大学 | 苯基四氮唑类xor抑制剂及其制备方法与应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2144533C1 (ru) * | 1994-12-09 | 2000-01-20 | Такеда Кемикал Индастриз, Лтд. | Производные тетразола, способ их получения и фармацевтические композиции на их основе |
| EP1127882A1 (en) * | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021556A (en) | 1972-06-08 | 1977-05-03 | Icn Pharmaceuticals, Inc. | Xanthine oxidase inhibitors |
| US4024253A (en) | 1973-04-20 | 1977-05-17 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Treatment of elevated histamine and uric acid levels |
| US4182764A (en) | 1973-10-11 | 1980-01-08 | Merck & Co., Inc. | Tetrazole derivatives of [1-oxo-2-aryl or thienyl-2-substituted-5-indanyloxy(or thio)]alkanoic acids |
| US4874777A (en) | 1987-04-10 | 1989-10-17 | Eli Lilly And Company | Leukotriene antagonists |
| US4845231A (en) | 1988-02-12 | 1989-07-04 | American Home Products Corporation | Tetrazoles and their use as hypoglycemic agents |
| FR2631827B1 (fr) | 1988-05-27 | 1992-03-27 | Delalande Sa | Nouveaux derives d'(hetero)aryl-5 tetrazole, leur procede de preparation et leur application en therapeutique |
| US5260322A (en) | 1990-10-08 | 1993-11-09 | Merck & Co., Inc. | Angiotension II antagonists in the treatment of hyperuricemia |
| US5591862A (en) | 1993-06-11 | 1997-01-07 | Takeda Chemical Industries, Ltd. | Tetrazole derivatives, their production and use |
| JP2002503202A (ja) | 1996-02-02 | 2002-01-29 | メルク エンド カンパニー インコーポレーテッド | 抗糖尿病薬 |
| AU9696198A (en) | 1997-10-17 | 1999-05-10 | Aventis Pharmaceuticals Products Inc. | Therapeutic uses of quinoline derivatives |
| RU2341513C2 (ru) | 2001-06-12 | 2008-12-20 | Веллстат Терапьютикс Корпорейшн | Соединения для лечения метаболических заболеваний |
| AU2003226094A1 (en) * | 2002-03-27 | 2003-10-13 | Smithkline Beecham Corporation | Compounds and methods |
| US7078423B2 (en) * | 2002-07-18 | 2006-07-18 | Inotek Pharmaceuticals Corporation | 5-Aryltetrazole compounds, compositions thereof, and uses therefor |
| US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
| JP2004197711A (ja) * | 2002-12-20 | 2004-07-15 | Honda Motor Co Ltd | 回転流体機械 |
| JP2007523842A (ja) * | 2003-03-11 | 2007-08-23 | ノボ ノルディスク アクティーゼルスカブ | 酸安定化されたインスリンを含有する薬学的製剤 |
| AR051780A1 (es) | 2004-11-29 | 2007-02-07 | Japan Tobacco Inc | Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos |
| US8829058B2 (en) | 2008-03-13 | 2014-09-09 | Wellstat Therapeutics Corporation | Compounds and method for reducing uric acid |
| MX2010011603A (es) | 2008-04-30 | 2011-01-25 | Wellstat Therapeutics Corp | Compuestos de tetrazol para reducir el acido urico. |
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2009
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- 2009-04-30 ES ES09739797.0T patent/ES2561039T3/es active Active
- 2009-04-30 CN CN2009801155473A patent/CN102014898B/zh not_active Expired - Fee Related
- 2009-04-30 BR BRPI0910541A patent/BRPI0910541B8/pt not_active IP Right Cessation
- 2009-04-30 CA CA2722624A patent/CA2722624C/en not_active Expired - Fee Related
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- 2009-04-30 WO PCT/US2009/042298 patent/WO2009134995A2/en not_active Ceased
- 2009-04-30 KR KR1020107024008A patent/KR101613611B1/ko not_active Expired - Fee Related
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2013
- 2013-03-04 US US13/783,680 patent/US8889724B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2144533C1 (ru) * | 1994-12-09 | 2000-01-20 | Такеда Кемикал Индастриз, Лтд. | Производные тетразола, способ их получения и фармацевтические композиции на их основе |
| EP1127882A1 (en) * | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2683570C1 (ru) * | 2018-05-23 | 2019-03-29 | Евгений Иванович Верещагин | Композиция из растительных компонентов, обладающая способностью снижать уровень мочевой кислоты сыворотки крови |
Also Published As
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| KR20100135851A (ko) | 2010-12-27 |
| JP2011519865A (ja) | 2011-07-14 |
| RU2010148762A (ru) | 2012-06-10 |
| WO2009134995A3 (en) | 2009-12-23 |
| MX2010011603A (es) | 2011-01-25 |
| ES2561039T3 (es) | 2016-02-24 |
| US8889724B2 (en) | 2014-11-18 |
| US8410154B2 (en) | 2013-04-02 |
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| EP2282736B1 (en) | 2015-11-11 |
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| AU2009243028B2 (en) | 2015-01-29 |
| US20130336949A1 (en) | 2013-12-19 |
| CN102014898B (zh) | 2013-01-23 |
| CN102014898A (zh) | 2011-04-13 |
| IL209004A0 (en) | 2011-01-31 |
| WO2009134995A2 (en) | 2009-11-05 |
| IL209004A (en) | 2014-04-30 |
| JP5431457B2 (ja) | 2014-03-05 |
| HK1147446A1 (en) | 2011-08-12 |
| NZ588374A (en) | 2012-11-30 |
| BRPI0910541B1 (pt) | 2019-12-03 |
| CA2722624C (en) | 2017-03-21 |
| US20110206653A1 (en) | 2011-08-25 |
| ZA201006929B (en) | 2011-06-29 |
| BRPI0910541B8 (pt) | 2021-05-25 |
| CA2722624A1 (en) | 2009-11-05 |
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